Regional Sales Director - 9758

InsuranceWorks.ca; Toronto; Remote; CAD 90,000 - 140,000; Full time

Job summary

A leading company in the insurance technology space is looking for a Regional Sales Director to spearhead growth across Eastern Canada. This fully remote role will leverage strong B2B sales experience within a collaborative culture. Candidates should possess in-depth market knowledge and a successful sales track record, enjoying autonomy and flexibility while shaping the future of insurance technology.

Benefits

Flexible compensation structure

Extended health, dental, and vision benefits

Extra time off

Professional development allowance

Employee and Family Assistance Program

Equity participation

Remote-first team culture

Qualifications

• 5+ years of B2B software sales, ideally in InsurTech.
• Strong understanding of the Canadian insurance market.
• Proven track record of generating and closing new business deals.
• Exceptional communication and presentation skills.

Responsibilities

• Drive adoption of the SaaS platform among insurers and brokers.
• Connect with senior decision-makers in the insurance industry.
• Contribute to scaling operations within a fast-paced environment.

Skills

B2B software sales

Insurance market understanding

Communication

Presentation skills

Goal-oriented

Education

5+ years of B2B software sales experience

Job description

Our client is seeking aRegional Sales Directorto help scale their modern SaaS platform within the Canadian insurance space. With a focus onEastern Canada, this fully remote role offer the chance to work at the forefront of insurance technology. The successful candidate will bring deep industry knowledge and strong B2B sales experience to help drive adoption of an all-in-one platform tailored for insurers, mutuals, MGAs, and brokerages.

This role is ideal for someone who thrives in a fast-paced environment, values flexibility, and is motivated by the opportunity to transform how the insurance industry operates.

The Employer:

Our client is a rapidly growing technology firm offering a configurable, all-in-one software solution built specifically for the insurance industry. With a strong reputation for innovation and customer focus, they’ve earned the trust of insurers and brokers across Canada. The company fosters a connected and collaborative culture—despite being fully remote—and is known for valuing initiative, transparency, and team success.

About You:

You’re a consultative sales professional with 5+ years of success in B2B software sales—ideally in the insurance or InsurTech space. You bring a deep understanding of insurance workflows and the ability to connect with senior decision-makers. You’re motivated by the chance to make a real impact, enjoy autonomy, and thrive in high-growth environments.

Necessary Qualifications Include:

5+ years of B2B software sales experience, preferably in InsurTech or related sectors

Strong understanding of the Canadian insurance market (carriers, mutuals, MGAs, brokers)

Proven track record of generating and closing new business deals

Exceptional presentation and communication skills

Ability to quickly learn and communicate complex software solutions

Self-starter with a performance-driven, goal-oriented mindset

Experience in a high-growth SaaS environment is a strong asset

What’s in It for You:

Flexible compensation structure (salary, commission, or blended)

Extended health, dental, and vision benefits

Extra time off beyond standard vacation and holidays

Professional development allowance

Employee and Family Assistance Program

Equity participation through Share Appreciation Rights

Collaborative, remote-first team culture with in-person connection opportunities

Chance to shape the future of insurance technology across Canada

About Us:

DGA Careershas been proudly serving the Canadian insurance industry for over 30 years, specializing in recruitment for insurers, brokerages, and InsurTech firms nationwide. With offices in Toronto, Vancouver, Montreal, Edmonton, and Calgary, we bring local insight and national reach to every search.

Interested candidates, please contact Kim Ehman at 587-885-1849 or email your resume in confidence to kim